Fluorescent dye oil tracer compositions

ABSTRACT

A composition includes a functionalized fluorescent dye. The functionalized fluorescent dye includes an isothiocyanate-containing compound functionalized with a functional group. The functional group includes a primary amine. The functionalized fluorescent dye can be mixed with a fluid to form a tracer fluid for tracing fluid flow in a subterranean formation.

TECHNICAL FIELD

This disclosure relates to methods and compositions used in generatingand using functionalized fluorescent tracers with barcoded structures indrilling and oil well applications.

BACKGROUND

Tracer techniques can be a powerful diagnostic tool in numerousscientific disciplines and for technologies in many industrial sectors.Molecular tracers can include water-soluble or oil-soluble compounds. Infield tests of oilfields, water-soluble tracers can provide a betterunderstanding of the studied oil reservoir, for example, a betterunderstanding of inter-well connections, connections between layers andheterogeneities. Similarly, oil-soluble tracers can provide informationon petroleum products, for example qualitative analysis of theproduction fluid return from multiple stage completions, either verticalor horizontal completions.

SUMMARY

This disclosure describes technologies relating to functionalizedfluorescent tracers with barcoded structures, methods of making thetracers, and methods of using the tracers. Certain aspects of thesubject matter described can be implemented as a composition. Thecomposition includes a functionalized fluorescent dye. Thefunctionalized fluorescent dye includes an isothiocyanate-containingcompound functionalized with a functional group. The functional groupincludes a primary amine. The isothiocyanate-containing compound isselected from the group consisting of methyl isothiocyanate, ethylisothiocyanate, propyl isothiocyanate, isopropyl isothiocyanate, butylisothiocyanate, tert-butyl isothiocyanate, hexyl isothiocyanate, octylisothiocyanate, decyl isothiocyanate, dodectyl isothiocyanate,tetradecyl isothiocyanate, hexadecyl isothiocyanate, octadecylisothiocyanate, phenyl isothiocyanate, benzyl isothiocyanate,phenylethyl isothiocyanate, cyclohexyl isothiocyanate, cyclohexylmethylisothiocyanate, 2-piperidinoethyl isothiocyanate, p-tolylisothiocyanate, 2,6-dimethylphenyl isothiocyanate, 4-ethylphenylisothiocyanate, 4-methoxyphenyl isothiocyanate, 2,4-dimethoxyphenylisothiocyanate, 4-chlorophenyl isothiocyanate, 2,6-dichlorophenylisothiocyanate, 2,4,5-trichlorophenyl isothiocyanate, 3-bromophenylisothiocyanate, 2,5-dibromophenyl isothiocyanate, 2,4,6-tribromophenylisothiocyanate, 3-fluorophenyl isothiocyanate, 2,6-difluorophenylisothiocyanate, 2,4,6-trifluorophenyl isothiocyanate,4-(trifluoromethyl)phenyl isothiocyanate, 3,5-bis(trifluoromethyl)phenylisothiocyanate, 2-chloro-5-(trifluoromethyl)phenyl isothiocyanate,4-bromo-2-(trifluoromethyl)phenyl isothiocyanate,4-fluoro-3-(trifluoromethyl)phenyl isothiocyanate,3-chloro-4-fluorophenyl isothiocyanate, 2-bromo-4-fluorophenylisothiocyanate, or 4-bromo-2-chlorophenyl isothiocyanate, or any isoformthereof. The functional group is selected from the group consisting of1-naphthylamine, 2-aminoanthracene, 1-aminopyrene, 6-chrysenamine,9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine,1,10-phenanthrolin-5-amine, 9H-carbazol-2-amine, or3-amino-9-ethylcarbazole.

This, and other aspects, can include one or more of the followingfeatures. The isothiocyanate-containing compound can be cyclohexylmethylisothiocyanate, and the functional group can be 1-naphthylamine. Theisothiocyanate-containing compound can be 2,6-difluorophenylisothiocyanate, and the functional group can be 2-aminoanthracene. Theisothiocyanate-containing compound can be 4-ethylphenyl isothiocyanate,and the functional group can be 1-aminopyrene. Theisothiocyanate-containing compound can be hexyl isothiocyanate, and thefunctional group can be 6-chyrsenamine. The isothiocyanate-containingcompound can be butyl isothiocyanate, and the functional group can be9-aminophenanthrene. The isothiocyanate-containing compound can be ethylisothiocyanate, and the functional group can be 1-aminofluorene. Theisothiocyanate-containing compound can be decyl isothiocyanate, and thefunctional group can be 9-aminoacridine. The isothiocyanate-containingcompound can be benzyl isothiocyanate, and the functional group can be1,10-phenanthrolin-5-amine. The isothiocyanate-containing compound canbe p-tolyl isothiocyanate, and the functional group can be3-amino-9-ethylcarbazole.

Certain aspects of the subject matter described can be implemented as amethod of making a functionalized fluorescent dye. The method includesdissolving an oil-soluble isothiocyanate-containing compound in a firstportion of a first organic solvent to yield a first solution. Theoil-soluble isothiocyanate-containing compound is selected from thegroup consisting of methyl isothiocyanate, ethyl isothiocyanate, propylisothiocyanate, isopropyl isothiocyanate, butyl isothiocyanate,tert-butyl isothiocyanate, hexyl isothiocyanate, octyl isothiocyanate,decyl isothiocyanate, dodectyl isothiocyanate, tetradecylisothiocyanate, hexadecyl isothiocyanate, octadecyl isothiocyanate,phenyl isothiocyanate, benzyl isothiocyanate, phenylethylisothiocyanate, cyclohexyl isothiocyanate, cyclohexylmethylisothiocyanate, 2-piperidinoethyl isothiocyanate, p-tolylisothiocyanate, 2,6-dimethylphenyl isothiocyanate, 4-ethylphenylisothiocyanate, 4-methoxyphenyl isothiocyanate, 2,4-dimethoxyphenylisothiocyanate, 4-chlorophenyl isothiocyanate, 2,6-dichlorophenylisothiocyanate, 2,4,5-trichlorophenyl isothiocyanate, 3-bromophenylisothiocyanate, 2,5-dibromophenyl isothiocyanate, 2,4,6-tribromophenylisothiocyanate, 3-fluorophenyl isothiocyanate, 2,6-difluorophenylisothiocyanate, 2,4,6-trifluorophenyl isothiocyanate,4-(trifluoromethyl)phenyl isothiocyanate, 3,5-bis(trifluoromethyl)phenylisothiocyanate, 2-chloro-5-(trifluoromethyl)phenyl isothiocyanate,4-bromo-2-(trifluoromethyl)phenyl isothiocyanate,4-fluoro-3-(trifluoromethyl)phenyl isothiocyanate,3-chloro-4-fluorophenyl isothiocyanate, 2-bromo-4-fluorophenylisothiocyanate, or 4-bromo-2-chlorophenyl isothiocyanate, or any isoformthereof. The method includes dissolving a functional group in a secondportion of the first organic solvent to yield a second solution. Thefunctional group includes a primary amine and is selected from the groupconsisting of 1-naphthylamine, 2-aminoanthracene, 1-aminopyrene,6-chrysenamine, 9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine,1,10-phenanthrolin-5-amine, 9H-carbazol-2-amine, or3-amino-9-ethylcarbazole. The method includes mixing the first solutionand the second solution to form a reaction mixture. The method includesextracting the functionalized fluorescent dye from the reaction mixture.The functionalized fluorescent dye is a reaction product of theoil-soluble isothiocyanate-containing compound and the functional group.

This, and other aspects, can include one or more of the followingfeatures. The first organic solvent can include methanol, ethanol,propanol, isopropanol, chloroform, dichloromethane, acetone,cyclohexane, hexane, benzene, toluene or any combination thereof.Extracting the functionalized fluorescent dye from the reaction mixturecan include evaporating the first organic solvent. The method caninclude re-dispersing the functionalized fluorescent dye in a secondorganic solvent after extracting the functionalized fluorescent dye fromthe reaction mixture. The second organic solvent can include crude oil,diesel, mineral oil, food oil, methanol, ethanol, propanol, isopropanol,butanol, pentanol, hexanol, heptanol, octenol, acetone, ethyl acetate,acetonitrile, chloroform, hexane, heptane, cyclohexane, benzene,toluene, tetrahydrofuran, or any combination thereof. The second organicsolvent can have a composition different from the composition of thefirst organic solvent.

Certain aspects of the subject matter described can be implemented as amethod of tracing fluid flow in a subterranean formation. The methodincludes mixing a functionalized fluorescent tracer and a fluid to forma tracer fluid. The functionalized fluorescent tracer includes anisothiocyanate-containing compound functionalized with a functionalgroup. The functional group includes a primary amine. Theisothiocyanate-containing compound is selected from the group consistingof methyl isothiocyanate, ethyl isothiocyanate, propyl isothiocyanate,isopropyl isothiocyanate, butyl isothiocyanate, tert-butylisothiocyanate, hexyl isothiocyanate, octyl isothiocyanate, decylisothiocyanate, dodectyl isothiocyanate, tetradecyl isothiocyanate,hexadecyl isothiocyanate, octadecyl isothiocyanate, phenylisothiocyanate, benzyl isothiocyanate, phenylethyl isothiocyanate,cyclohexyl isothiocyanate, cyclohexylmethyl isothiocyanate,2-piperidinoethyl isothiocyanate, p-tolyl isothiocyanate,2,6-dimethylphenyl isothiocyanate, 4-ethylphenyl isothiocyanate,4-methoxyphenyl isothiocyanate, 2,4-dimethoxyphenyl isothiocyanate,4-chlorophenyl isothiocyanate, 2,6-dichlorophenyl isothiocyanate,2,4,5-trichlorophenyl isothiocyanate, 3-bromophenyl isothiocyanate,2,5-dibromophenyl isothiocyanate, 2,4,6-tribromophenyl isothiocyanate,3-fluorophenyl isothiocyanate, 2,6-difluorophenyl isothiocyanate,2,4,6-trifluorophenyl isothiocyanate, 4-(trifluoromethyl)phenylisothiocyanate, 3,5-bis(trifluoromethyl)phenyl isothiocyanate,2-chloro-5-(trifluoromethyl)phenyl isothiocyanate,4-bromo-2-(trifluoromethyl)phenyl isothiocyanate,4-fluoro-3-(trifluoromethyl)phenyl isothiocyanate,3-chloro-4-fluorophenyl isothiocyanate, 2-bromo-4-fluorophenylisothiocyanate, or 4-bromo-2-chlorophenyl isothiocyanate, or any isoformthereof. The functional group is selected from the group consisting of1-naphthylamine, 2-aminoanthracene, 1-aminopyrene, 6-chrysenamine,9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine,1,10-phenanthrolin-5-amine, 9H-carbazol-2-amine, or3-amino-9-ethylcarbazole. The method includes flowing the tracer fluidinto a first subterranean formation. The method includes recovering asample from the first subterranean formation or a second subterraneanformation connected to the first subterranean formation. The methodincludes analyzing the sample for a fluorescent signal.

This, and other aspects, can include one or more of the followingfeatures. The method can include identifying the functionalizedfluorescent tracer in the sample using fluorescence, ultraviolet-visible(UV-Vis) spectroscopy, Fourier-transform infrared spectroscopy (FTIR),Raman spectroscopy, mass spectroscopy (MS), high performance liquidchromatography (HPLC), or liquid chromatography-mass spectroscopy(LC-MS), or any combination thereof. The sample can be a fluid sample.The sample can be a solid sample. The fluid can be a fracking fluid. Thefluid can be a drilling mud. The method can include analyzing the samplefor a barcode structure. The method can include identifying theisothiocyanate-containing compound of the functionalized fluorescenttracer based on the barcode structure.

The details of one or more implementations of the subject matter of thisdisclosure are set forth in the accompanying drawings and thedescription. Other features, aspects, and advantages of the subjectmatter will become apparent from the description, the drawings, and theclaims.

DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic diagram of an example well.

FIG. 2 is a flow chart of an example method for making a functionalizedfluorescent dye that can be used in the well of FIG. 1 .

FIG. 3 is a flow chart of an example method for treating a well.

FIG. 4 is a molecular structure of an example functionalized fluorescentdye.

FIG. 5 is a molecular structure of an example functionalized fluorescentdye.

FIG. 6 is a molecular structure of an example functionalized fluorescentdye.

FIG. 7 is a molecular structure of an example functionalized fluorescentdye.

FIG. 8 is a molecular structure of an example functionalized fluorescentdye.

FIG. 9 is a molecular structure of an example functionalized fluorescentdye.

FIG. 10 is a molecular structure of an example functionalizedfluorescent dye.

FIG. 11 is a molecular structure of an example functionalizedfluorescent dye.

FIG. 12 is a molecular structure of an example functionalizedfluorescent dye.

DETAILED DESCRIPTION

This disclosure describes functionalized fluorescent tracers, methods ofmaking the tracers, and methods of using the tracers. The functionalizedfluorescent tracers can be used, for example, to track hydrocarbons inwells. A chemical method can be implemented to modify the structures ofconventional fluorescent dye molecules by covalently bonding an aromaticcompound to the dye molecule, which can increase the fluorescent dye'shydrophobicity. The resulting dye is oil-soluble while retaining itsfluorescence. The aromatic compound can also serve as a molecularidentifier.

FIG. 1 depicts an example of a drilling operation 10 for a well 12. Thewell 12 can be in a wellbore 20 formed in a subterranean zone 14 of ageological formation in the Earth's crust. The well 12 enables access tothe subterranean zone 14 to allow recovery (that is, production) offluids to the surface and, in some implementations, additionally oralternatively allows fluids to be placed in the Earth. The subterraneanzone 14 can include, for example, a formation, a portion of a formation,or multiple formations in a hydrocarbon-bearing reservoir from whichrecovery operations can be practiced to recover trapped hydrocarbons.Examples of unconventional reservoirs include tight-gas sands, gas andoil shales, coalbed methane, heavy oil and tar sands, gas-hydratedeposits, to name a few. In some implementations, the subterranean zone14 includes an underground formation including natural fractures 60 inrock formations containing hydrocarbons (for example, oil, gas, orboth). For example, the subterranean zone 14 can include a fracturedshale. In some implementations, the well 12 can intersect other suitabletypes of formations, including reservoirs that are not naturallyfractured.

The well 12 can include a casing 22 and well head 24. The wellbore 20can be a vertical, horizontal, deviated, or multilateral bore. Thecasing 22 can be cemented or otherwise suitably secured in the wellbore20. Perforations 26 can be formed in the casing 22 at the level of thesubterranean zone 14 to allow oil, gas, and by-products to flow into thewell 12 and be produced to the surface 25. Perforations 26 can be formedusing shape charges, a perforating gun, or otherwise.

For a drilling treatment 10, a work string 30 can be disposed in thewellbore 20. The work string 30 can be coiled tubing, sectioned pipe, orother suitable tubing. A drilling tool or drill bit 32 can be coupled toan end of the work string 30. Packers 36 can seal an annulus 38 of thewellbore 20 uphole of and downhole of the subterranean zone 14. Packers36 can be mechanical, fluid inflatable, or other suitable packers.

One or more pump trucks 40 can be coupled to the work string 30 at thesurface 25. The pump trucks 40 pump drilling mud 58 down the work string30 to lubricate and cool the drilling tool or drill bit 32, maintainhydrostatic pressure in the wellbore, and carry subterranean cuttings tothe surface. The drilling mud 58 can include a fluid pad, proppants,flush fluid, or a combination of these components. The pump trucks 40can include mobile vehicles, equipment such as skids, or other suitablestructures.

One or more instrument trucks 44 can also be provided at the surface 25.The instrument truck 44 can include a drilling control system 46 and adrilling simulator 47. The drilling control system 46 monitors andcontrols the drilling treatment 10. The drilling control system 46 cancontrol the pump trucks 40 and fluid valves to stop and start thedrilling treatment 10. The drilling control system 46 communicates withsurface and subsurface instruments to monitor and control the drillingtreatment 10. In some implementations, the surface and subsurfaceinstruments may comprise surface sensors 48, down-hole sensors 50, andpump controls 52.

Additives 81 can be mixed with drilling mud 58 or other drilling fluidsand flowed through the reservoir. In some implementations, the additives81 can include one or more tracers, for example, a fluorescent dye.Fluorescent dyes can be used as oil-soluble tracers. These dyes areinexpensive and easy to use. Examples of fluorescent dyes includefluorescein, eosin, Rhodamine, and Rhodamine-B. However, these organicdye-based tracers have some shortcomings as oil-soluble tracers. Forexample, the water-soluble tracers fluorescein, eosin, and Rhodamine canadsorb onto reservoir rock or partition with the oil phase. In oil,these tracers have poor solubility due to their high hydrophilicity,although the molecules may partially dissolve in the oil phase. Inaddition, the number of tracers is limited to the number of organic dyemolecules available.

The tracers described herein overcome these shortcomings. These tracerscan be generated using a synthetic method to chemically modify themolecular structure of a dye. For example, by covalently graftingfunctional groups onto the dye molecules, the various functional groupscan create barcoded structural information, resulting in new compounds.In some embodiments, by introducing hydrophobic functional groups (forexample, an aromatic functional group), the hydrophobicity of theresulting molecules can be enhanced, thus improving their solubility inan oil phase. By tailoring the molecules, the hydrophobicity of themolecule can be adjusted to a desired degree. Therefore, the partitionof the molecule in an oil phase is controllable. This, in part, enablesthe potential application of these functionalized fluorescent dyes aspartition tracers for oil reservoir applications. The structure-modifieddyes reserve their fluorescence properties, although in someimplementations the fluorescence features may also be modified by theintroduction of functional groups.

These functionalized fluorescent dyes are described herein as barcodedor having barcode information. In this context, “barcode” refers to thefact that these functionalized dyes or tracers are uniquely identifiabletwo or more orthogonal analyses. As a first factor, the tracers can beidentified by their fluorescence signal, for example, by the wavelengthof the emission spectrum or simply by the presence of a fluorescentsignal. As a second factor, the tracers can be identified by their massor hydrophobicity. Accordingly, the unique combinations of the differentfluorophores and the different functionalization groups results in alibrary of barcoded tracers.

Barcoded tracers have several advantages. For example, differentcombinations of different tracers can be used simultaneously or inparallel to provide information about drilling operations orsubterranean formations. For example, two or more uniquely identifiabletracers can be injected at two or more different drilling sites and canyield information about inter well connectivity. In another example,uniquely identifiable tracers can be injected at the same drilling siteat different times, can yield temporal information about transit time,depth, or length of subterranean fractures or formations.

Further, the two-factor nature of the barcode tracers allows for anadvantageous two-factor analysis. The first factor, the fluorescencesignal, can be detected in an initial, rapid analysis. Accordingly,samples recovered from a drilling operation or subterranean formationcan be quickly and qualitative analyzed for the presence of afluorescence signal, i.e., a ‘yes/no’ analysis. In some implementations,this first analysis can be done on-site, and samples exhibiting afluorescence signal can be allocated for further processing. Next, thesamples exhibiting a fluorescence signal can be subsequently separatedand analyzed by mass or chromatographic methods, for example by highperformance liquid chromatography (HPLC), mass spectrometry (MS), orliquid chromatography-mass spectrometry (LC-MS) analysis.

A chemical method to modify the structures of conventional dye moleculesby introducing molecular barcode information and by tailoring thehydrophobicity of the dye molecules is described herein. The resultingcompounds expand the number of dyes available for tracer applications asoil tracers or partition tracers.

The new dye molecules include substituted thioureas represented by thegeneral structure of the reaction product shown in Equation 1. As shownin Equation 1, the new dye molecules can be synthesized by reacting anisothiocyanate (R₁—NCS) with a primary amine (R_(II)—NH₂). The R_(I)group is a hydrophobic group which can be aliphatic or aromatic. In thegeneral structure, R_(I) can be selected from the group that includeshydrogen, alkoxy, haloalkoxy (including Cl, Br, or I), aryl, orheteroaryl (including N, NH, O, or S). The R_(I) group confers amolecular fingerprint or barcode structure into the new dye molecules.The R_(I) group is a hydrophobic aromatic group that is fluorescent. TheR_(I) group can be detectable by optical methods, for example,fluorescence imaging or molecular spectroscopy (absorbance orfluorescence). The substituted thioureas (new dye molecules) aredetectable by spectroscopy methods, for example, UV Visible spectroscopy(UV-Vis), fluorescence, Fourier-transform infrared spectroscopy (FTIR),Raman spectroscopy, mass spectroscopy, or chromatography (such as HPLCor LC-MS).

FIG. 2 is a flow chart of an example method 200 of making afunctionalized fluorescent dye. The functionalized fluorescent dye canbe used, for example, to trace an oil phase in a subterranean formation.Method 200 can be implemented to form a substituted thiourea (reactionproduct of Equation 1). The reactions were performed at room temperaturein an organic solvent. At block 202, an oil-solubleisothiocyanate-containing compound is dissolved in a first portion ofthe organic solvent to yield a first solution. The oil-solubleisothiocyanate-containing compound can be considered a barcode that canbe detected and used to identify the functionalized fluorescent dye thatis to be formed and used as an oil tracer. At block 204, anaromatic/heterocyclic compound including a primary amino group isdissolved in a second portion of the organic solvent to yield a secondsolution. The aromatic/heterocyclic compound at block 204 is a primaryamine. The aromatic/heterocyclic compound at block 204 is a fluorophore.The organic solvent at blocks 202 and 204 is any organic solvent inwhich both the oil-soluble isothiocyanate-containing compound and thearomatic/heterocyclic compound are soluble. For example, the organicsolvent at blocks 202 and 204 is methanol, ethanol, propanol,isopropanol, chloroform, dichloromethane, acetone, cyclohexane, hexane,benzene, or toluene. The first solution and the second solution eachcontain the same molecular molar concentration of the oil-solubleisothiocyanate-containing compound and the aromatic/heterocycliccompound, respectively. At block 206, the first solution and the secondsolution are mixed to form a reaction mixture. In some implementations,the first solution and the second solution are mixed in equal volumes atblock 206 and stirred vigorously. In some implementations, the reactionbetween the oil-soluble isothiocyanate-containing compound and thearomatic/heterocyclic compound is allowed to continue while stirring forat least 12 hours, at least 14 hours, at least 16 hours, at least 18hours, at least 20 hours, at least 22 hours, or at least 24 hours atblock 206. At block 208, a functionalized fluorescent dye is extractedfrom the reaction mixture. The functionalized fluorescent dye extractedat block 208 is a reaction product of the oil-solubleisothiocyanate-containing compound and the aromatic/heterocycliccompound including the primary amino group. The functionalizedfluorescent dye extracted at block 208 is the new dye molecule that canbe used as an oil tracer. In some implementations, extracting thefunctionalized fluorescent dye from the reaction mixture at block 208includes evaporating the organic solvent by nitrogen bubbling, heating,rotary evaporation, or a combination of these. The obtained solid powder(functionalized fluorescent dye) can be re-dispersed into a differentorganic solvent, such as crude oil, diesel, mineral oil, food oil,methanol, ethanol, propanol, isopropanol, butanol, pentanol, hexanol,heptanol, octenol, acetone, ethyl acetate, acetonitrile, chloroform,hexane, heptane, cyclohexane, benzene, toluene, tetrahydrofuran, or anycombination of these.

Table 1 illustrates different oil-soluble isothiocyanate-containingcompounds. The compounds shown in Table 1 include different alkylfunctional groups. The oil-soluble isothiocyanate-containing compound(used in block 202 of method 200) can be selected from any of thecompounds shown in Table 1. R_(I)—NCS for forming a substituted thioruea(reaction product of Equation 1) can be selected from any of thecompounds shown in Table 1.

TABLE 1 Isothiocyanate-containing Compounds with Alkyl Functional GroupsCompound Molecular Structure/Weight (Daltons) CAS number Methylisothiocyanate

556-61-6 Ethyl isothiocyanate

542-85-8 Propyl isothiocyanate

628-30-8 Isopropyl isothiocyanate

2253-73-8 Butyl isothiocyanate

592-82-5 Tert-butyl isothiocyanate

590-42-1 Hexyl isothiocyanate

4404-45-9 Octyl isothiocyanate

4430-45-9 Decyl isothiocyanate

24540-94-1_([PH1]) Dodecyl isothiocyanate

1072-32-8_([PH2]) Tetradecyl isothiocyanate

3224-48-4_([PH3]) Hexadecyl isothiocyanate

4426-87-3_([PH4]) Octadecyl isothiocyanate

2877-26-1_([PH5])

Table 2 illustrates different oil-soluble isothiocyanate-containingcompounds. The compounds shown in Table 2 include different cyclicgroups. The cyclic groups can be aromatic or non-aromatic. Theoil-soluble isothiocyanate-containing compound (used in block 202 ofmethod 200) can be selected from any of the compounds shown in Table 2.R_(I)—NCS for forming a substituted thioruea (reaction product ofEquation 1) can be selected from any of the compounds shown in Table 2.

TABLE 2 Isothiocyanate-containing Compounds with Cyclic Groups CASCompound Molecular Structure/Weight (Daltons) number Phenylisothiocyanate

103- 72-0 Benzyl isothiocyanate

622- 78-6 Phenylethyl isothiocyanate

2257- 09-2 Cyclohexyl isothiocyanate

1122- 82-3 Cyclohexylmethyl isothiocyanate

52395- 66-1 2-piperidinoethyl isothiocyanate

32813- 24-4 p-Tolyl isothiocyanate

622- 59-3 2,6-dimethylphenyl isothiocyanate

19241- 16-8 4-ethylphenyl isothiocyanate

18856- 63-8 4-methoxyphenyl isothiocyanate

2284- 20-0 2,4- dimethoxyphenyl isothiocyanate

33904- 03-9 4-chlorophenyl isothiocyanate

2131- 55-7 2,6-dichlorophenyl isothiocyanate

6590- 95-0 2,4,5- trichlorophenyl isothiocyanate

23165- 46-0 3-bromophenyl isothiocyanate

2131- 59-1 2,5-dibromophenyl isothiocyanate

98041- 67-9 2,4,6- tribromophenyl isothiocyanate

22134- 11-8 3-fluorophenyl isothiocyanate

404- 72-8 2,6-difluorophenyl isothiocyanate

207974- 17-2 2,4,6- trifluorophenyl isothiocyanate

206761- 91-3 4-(Trifluoro- methyl) phenyl isothiocyanate

1645- 65-4 3,5-Bis (trifluoromethyl) phenyl isothiocyanate

23165- 29-9 2-Chloro-5- (trifluoromethyl) phenyl isothiocyanate

23165- 49-3 4-Bromo-2- (trifluoromethyl) phenyl isothiocyanate

206559- 46-8 4-Fluoro-3- (trifluoromethyl) phenyl isothiocyanate

302912- 43-2 3-Chloro-4- fluorophenyl isothiocyanate

137724- 66-4 2-Bromo-4- fluorophenyl isothiocyanate

183995- 72-4 4-Bromo-2- chlorophenyl isothiocyanate

98041- 69-1

Table 3 illustrates different aromatic amine-containing functionalgroups that can be used to functionalize an isothiocyanate-containingcompound. The compounds shown in Table 3 are aromatic or heterocycliccompounds with primary amino groups. The aromatic/heterocyclic compoundincluding the primary amino group (used in block 204 of method 200) canbe selected from any of the compounds shown in Table 3. R_(I)—NH₂ forforming a substituted thioruea (reaction product of Equation 1) can beselected from any of the compounds shown in Table 3. The compounds havedifferent molecular weights and provide both barcode information and theability to tailor the hydrophobicity and miscibility with oils of theresulting compound, based on, for example, the number of cyclic rings.Accordingly, isothiocyanate-containing compounds functionalized with thecompounds listed in Table 3 can have variable partitioning in oilphases.

TABLE 3 Aromatic Compounds with Primary Amino Groups Compound MolecularStructure/Weight (Daltons) CAS number 1-naphthylamine

134-32-7 2-aminoanthracene

613-13-8 1-aminopyrene

1606-67-3 6-chrysenamine

2642-98-0 9-aminophenanthrene

947-73-9 2-aminofluorene

153-78-6 9-aminoacridine

90-45-9 1,10-phenanthrolin-5-amine

54258-41-2 9H-carbazol-2-amine (hydrochloride)

63716-35-8 3-amino-9-ethylcarbazole

132-32-1

The dyes described herein can be used as tracers in subterraneanapplications. For example, multistage hydraulic fracturing along ahorizontal well is key to effectively recover hydrocarbons from tightreservoirs. Improving the hydrocarbon recovery requires detailedproduction information of each hydraulic fracture. Water-solublechemical tracers are often used to calculate the production profile frommultistage fracturing through a tracer flow back test, whereasoil-soluble tracers are used as a direct indicator to estimate the oilproduction contribution in individual fractures stages, for example,diagnosis of multi-zone oil flow efficiency, confirming zonal oil flow,or qualifying flow assurance. Oil-soluble tracers can also be embeddedin the porous media and absorbed on the surfaces of solid carriers,which allows the tracers to be released from their carriers when oilpasses through and has negligible partitioning into the water or gasphase.

With the barcoded oil-soluble tracers described herein, qualitativeanalysis by fluorescence spectroscopy or imaging can be used for earlyscreening if the tracer is in the oil flow from each stage, whiledetailed molecular barcode information can be revealed by HPLC or LC-MSanalysis to identify each tracers from different locations. Further,these synthesized barcoded oil-soluble compounds can also be added tomud formulations in drilling fluids as mud tracers for mud loggingapplications.

FIG. 3 is a flow chart of an example method 300 of tracing fluid flow ina subterranean formation. At 302, a functionalized fluorescent tracer(such as the functionalized fluorescent tracer formed by method 200) anda fluid are mixed to form a tracer fluid. At 304, the tracer fluid isflowed into a first subterranean formation. At 306, a sample isrecovered from the first subterranean formation or a second subterraneanformation connected to the first subterranean formation. At 308, thesample is analyzed for a fluorescent signal. At block 310, the sample isanalyzed for a barcode structure. Once the barcode structure isdetermined based on analysis of the sample at block 310, the specifictracer that was used (for example, at blocks 302 and 304) can beidentified based on the determined barcode structure.

Example 1

1.43 grams (g) of 1-naphthylamine (Sigma-Aldrich, >99%, MW=143.18) wasdissolved in 50 milliliters (mL) of chloroform. 1.55 g ofcyclohexylmethyl isothiocyanate (TCI, >98%, MW=155.26) was separatelydissolved in 50 mL of chloroform. The two solutions were mixed in around bottom flask and reacted for more than 24 hours under vigorousstirring by a magnetic stirrer. Assuming all molecules were conjugatedto non-symmetrical aliphatic thioureas, the reaction product was anN-(1-naphthylene)-N′-cyclohexylmethylthiourea compound with a nominalconcentration of 0.1 molar (M) in chloroform solution. Upon completionof the reaction, the chloroform was evaporated by nitrogen blowdown, andthe solid powder sample was collected for further re-dissolving in adifferent organic solvent. The molecular structure of the functionalizedfluorescent dye is shown in FIG. 4 .

Example 2

1.93 g of 2-aminoanthracene (Alfa Aesar, 94%, MW=193.24) was dissolvedin 50 mL of acetone. 1.71 g of 2,6-difluorophenyl isothiocyanate (AlfaAesar, 97%, MW=171.17) was separately dissolved in 50 mL of acetone. Thetwo solutions were mixed in a round bottom flask and reacted for morethan 24 hours under vigorous stirring by a magnetic stirrer. Assumingall molecules were conjugated to non-symmetrical aromatic thioureas, thereaction product was an N-(2-anthracene)-N′-(2,6-difluorophenyl)thioureacompound with a nominal concentration of 0.1 M in acetone solution. Uponcompletion of the reaction, the acetone was evaporated by nitrogenblowdown, and the solid powder sample was collected for furtherre-dissolving in a different organic solvent. The molecular structure ofthe functionalized fluorescent dye is shown in FIG. 5 .

Example 3

2.17 g of 1-aminopyrene (TCI, >98%, MW=217.26) was dissolved in 50 mL ofacetone. 1.63 g of 4-ethylphenyl isothiocyanate (Alfa Aesar, 97%,MW=163.24) was separately dissolved in 50 mL of acetone. The twosolutions were mixed in a round bottom flask and reacted for more than24 hours under vigorous stirring by a magnetic stirrer. Assuming allmolecules were conjugated to non-symmetrical aromatic thioureas, thereaction product was an N-(1-pyrene)-N′-(4-ethylbenzyl)thiourea compoundwith a nominal concentration of 0.1 M in acetone solution. Uponcompletion of the reaction, the acetone was evaporated by nitrogenblowdown, and the solid powder sample was collected for furtherre-dissolving in a different organic solvent. The molecular structure ofthe functionalized fluorescent dye is shown in FIG. 6 .

Example 4

2.43 g of 6-chrysenamine (Sigma-Aldrich, 95%, MW=243.3) was dissolved in50 mL of acetone. 1.43 g of hexyl isothiocyanate (Alfa Aesar, 97%,MW=143.25) was separately dissolved in 50 mL of acetone. The twosolutions were mixed in a round bottom flask and reacted for more than24 hours under vigorous stirring by a magnetic stirrer. Assuming allmolecules were conjugated to aromatic-aliphatic thioureas, the reactionproduct was an N-(6-chrysene)-N′-hexylthiourea compound with a nominalconcentration of 0.1 M in acetone solution. Upon completion of thereaction, the acetone was evaporated by nitrogen blowdown, and the solidpowder sample was collected for further re-dissolving in a differentorganic solvent. The molecular structure of the functionalizedfluorescent dye is shown in FIG. 7 .

Example 5

1.93 g of 9-aminophenanthrene (Alfa Aesar, 96%, MW=193.24) was dissolvedin 50 mL of chloroform. 1.15 g of butyl isothiocyanate (MatrixScientific, 99%, MW=115.2) was separately dissolved in 50 mL ofchloroform. The two solutions were mixed in a round bottom flask andreacted for more than 24 hours under vigorous stirring by a magneticstirrer. Assuming all molecules were conjugated to aromatic-aliphaticthioureas, the reaction product was anN-(9-phenanthrene)-N′-butylthiourea compound with a nominalconcentration of 0.1 M in chloroform solution. Upon completion of thereaction, the chloroform was evaporated by nitrogen blowdown, and thesolid powder sample was collected for further re-dissolving in adifferent organic solvent. The molecular structure of the functionalizedfluorescent dye is shown in FIG. 8 .

Example 6

2.17 g of 1-aminofluorene (TCI, >98%, MW=181.23) was dissolved in 50 mLof ethanol. 0.87 g of ethyl isothiocyanate (Alfa Aesar, 97%, MW=87.15)was separately dissolved in 50 mL of ethanol. The two solutions weremixed in a round bottom flask and reacted for more than 24 hours undervigorous stirring by a magnetic stirrer. Assuming all molecules wereconjugated to aromatic-aliphatic thioureas, the reaction product was anN-(1-fluorene)-N′-ethylthiourea compound with a nominal concentration of0.1 M in ethanol solution. Upon completion of the reaction, the ethanolwas evaporated by nitrogen blowdown, and the solid powder sample wascollected for further re-dissolving in a different organic solvent. Themolecular structure of the functionalized fluorescent dye is shown inFIG. 9 .

Example 7

1.94 g of 9-aminoacridine (TCI, >97%, MW=194.24) was dissolved in 50 mLof ethanol. 1.99 g of decyl isothiocyanate (Matrix Scientific, 99%,MW=199.36) was separately dissolved in 50 mL of ethanol. The twosolutions were mixed in a round bottom flask and reacted for more than24 hours under vigorous stirring by a magnetic stirrer. Assuming allmolecules were conjugated to aromatic-aliphatic thioureas, the reactionproduct was an N-(9-acridine)-N′-decylthiourea compound with a nominalconcentration of 0.1 M in ethanol solution. Upon completion of thereaction, the ethanol was evaporated by nitrogen blowdown, and the solidpowder sample was collected for further re-dissolving in a differentorganic solvent. The molecular structure of the functionalizedfluorescent dye is shown in FIG. 10 .

Example 8

1.95 g of 1,10-phenanthrolin-5-amine (AmBeed, 98%, MW=195.22) wasdissolved in 50 mL of ethanol. 1.49 g of benzyl isothiocyanate (AcrosOrganics, 98%, MW=149.21) was separately dissolved in 50 mL of ethanol.The two solutions were mixed in a round bottom flask and reacted formore than 24 hours under vigorous stirring by a magnetic stirrer.Assuming all molecules were conjugated to non-symmetrical aromaticthioureas, the reaction product was anN-(5-(1,10-phenanthroline))-N′-benzylthiourea compound with a nominalconcentration of 0.1 M in ethanol solution. Upon completion of thereaction, the ethanol was evaporated by nitrogen blowdown, and the solidpowder sample was collected for further re-dissolving in a differentorganic solvent. The molecular structure of the functionalizedfluorescent dye is shown in FIG. 11 .

Example 9

2.10 g of 3-amino-9-ethylcarbazole (Acros Organics, 90% Tech, MW=210.27)was dissolved in 50 mL of chloroform. 1.49 g of p-tolyl isothiocyanate(Sigma-Aldrich, 97%, MW=149.21) was separately dissolved in 50 mL ofchloroform. The two solutions were mixed in a round bottom flask andreacted for more than 24 hours under vigorous stirring by a magneticstirrer. Assuming all molecules were conjugated to non-symmetricalaromatic thioureas, the reaction product was anN-(3-(9-ethylcarbazole))-N′-tolylthiourea compound with a nominalconcentration of 0.1 M in chloroform solution. Upon completion of thereaction, the chloroform was evaporated by nitrogen blowdown, and thesolid powder sample was collected for further re-dissolving in adifferent organic solvent. The molecular structure of the functionalizedfluorescent dye is shown in FIG. 12 .

Examples 1, 2, 3, 4, 5, 6, 7, 8, and 9 provide example procedures formaking a functionalized fluorescent dye. With similar procedures, anyone of the isothiocyanate-containing compounds shown in Table 1 can becombined with any one of the aromatic compounds with primary aminogroups shown in Table 3. With similar procedures, any one of theisothiocyanate-containing compounds shown in Table 2 can be combinedwith any one of the aromatic compounds with primary amino groups shownin Table 3. The following two paragraphs include example combinations ofisothiocyanate-containing compounds and aromatic compounds with primaryamino groups that can be combined to make a functionalized fluorescentdye.

Methyl isothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. Methyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. Methyl isothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. Methyl isothiocyanate and 6-chrysenaminecan be combined to make a functionalized fluorescent dye. Methylisothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. Methyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. Methyl isothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Methyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Methyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Methyl isothiocyanate and 3-amino-9-ethylcarbazole can be combinedto make a functionalized fluorescent dye. Ethyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. Ethyl isothiocyanate and 2-aminoanthracene can be combined to makea functionalized fluorescent dye. Ethyl isothiocyanate and 1-aminopyrenecan be combined to make a functionalized fluorescent dye. Ethylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Ethyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Ethyl isothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. Ethyl isothiocyanate and 9-aminoacridinecan be combined to make a functionalized fluorescent dye. Ethylisothiocyanate and 1,10-phenanthrolin-5-amine can be combined to make afunctionalized fluorescent dye. Ethyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. Ethyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Propyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Propyl isothiocyanateand 2-aminoanthracene can be combined to make a functionalizedfluorescent dye. Propyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. Propyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.Propyl isothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. Propyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. Propyl isothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Propyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Propyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Propyl isothiocyanate and 3-amino-9-ethylcarbazole can be combinedto make a functionalized fluorescent dye. Isopropyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. Isopropyl isothiocyanate and 2-aminoanthracene can be combined tomake a functionalized fluorescent dye. Isopropyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Isopropyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Isopropyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Isopropyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Isopropyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Isopropyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Isopropylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Isopropyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Butyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Butyl isothiocyanateand 2-aminoanthracene can be combined to make a functionalizedfluorescent dye. Butyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. Butyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.Butyl isothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. Butyl isothiocyanate and 2-aminofluorenecan be combined to make a functionalized fluorescent dye. Butylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Butyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Butyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Butyl isothiocyanate and 3-amino-9-ethylcarbazole can be combinedto make a functionalized fluorescent dye. Tert-butyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. Tert-butyl isothiocyanate and 2-aminoanthracene can be combined tomake a functionalized fluorescent dye. Tert-butyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Tert-butyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Tert-butyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Tert-butyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Tert-butyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Tert-butyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Tert-butylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Tert-butyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Hexyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Hexyl isothiocyanateand 2-aminoanthracene can be combined to make a functionalizedfluorescent dye. Hexyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. Hexyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.Hexyl isothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. Hexyl isothiocyanate and 2-aminofluorenecan be combined to make a functionalized fluorescent dye. Hexylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Hexyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Hexyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Hexyl isothiocyanate and 3-amino-9-ethylcarbazole can be combinedto make a functionalized fluorescent dye. Octyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. Octyl isothiocyanate and 2-aminoanthracene can be combined to makea functionalized fluorescent dye. Octyl isothiocyanate and 1-aminopyrenecan be combined to make a functionalized fluorescent dye. Octylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Octyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Octyl isothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. Octyl isothiocyanate and 9-aminoacridinecan be combined to make a functionalized fluorescent dye. Octylisothiocyanate and 1,10-phenanthrolin-5-amine can be combined to make afunctionalized fluorescent dye. Octyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. Octyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Decyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Decyl isothiocyanateand 2-aminoanthracene can be combined to make a functionalizedfluorescent dye. Decyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. Decyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.Decyl isothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. Decyl isothiocyanate and 2-aminofluorenecan be combined to make a functionalized fluorescent dye. Decylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Decyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Decyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Decyl isothiocyanate and 3-amino-9-ethylcarbazole can be combinedto make a functionalized fluorescent dye. Dodecyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. Dodecyl isothiocyanate and 2-aminoanthracene can be combined tomake a functionalized fluorescent dye. Dodecyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Dodecyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Dodecyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Dodecyl isothiocyanate and 2-aminofluorene can be combined to makea functionalized fluorescent dye. Dodecyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Dodecyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Dodecylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Dodecyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Tetradecyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Tetradecylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. Tetradecyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Tetradecyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Tetradecyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Tetradecyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Tetradecyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Tetradecyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Tetradecylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Tetradecyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Hexadecyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Hexadecylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. Hexadecyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Hexadecyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Hexadecyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Hexadecyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Hexadecyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Hexadecyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Hexadecylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Hexadecyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Octadecyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Octadecylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. Octadecyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Octadecyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Octadecyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Octadecyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Octadecyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Octadecyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Octadecylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Octadecyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye.

Phenyl isothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. Phenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. Phenyl isothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. Phenyl isothiocyanate and 6-chrysenaminecan be combined to make a functionalized fluorescent dye. Phenylisothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. Phenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. Phenyl isothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Phenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Phenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Phenyl isothiocyanate and 3-amino-9-ethylcarbazole can be combinedto make a functionalized fluorescent dye. Benzyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. Benzyl isothiocyanate and 2-aminoanthracene can be combined to makea functionalized fluorescent dye. Benzyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Benzyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Benzyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Benzyl isothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. Benzyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Benzyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Benzyl isothiocyanateand 9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. Benzyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Phenylethyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Phenylethylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. Phenylethyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Phenylethyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Phenylethyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Phenylethyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Phenylethyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Phenylethyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Phenylethylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Phenylethyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Cyclohexyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. Cyclohexylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. Cyclohexyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Cyclohexyl isothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. Cyclohexyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. Cyclohexyl isothiocyanate and 2-aminofluorene can be combined tomake a functionalized fluorescent dye. Cyclohexyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. Cyclohexyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. Cyclohexylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. Cyclohexyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. Cyclohexylmethyl isothiocyanate and 1-naphthylamine canbe combined to make a functionalized fluorescent dye. Cyclohexylmethylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. Cyclohexylmethyl isothiocyanate and1-aminopyrene can be combined to make a functionalized fluorescent dye.Cyclohexylmethyl isothiocyanate and 6-chrysenamine can be combined tomake a functionalized fluorescent dye. Cyclohexylmethyl isothiocyanateand 9-aminophenanthrene can be combined to make a functionalizedfluorescent dye. Cyclohexylmethyl isothiocyanate and 2-aminofluorene canbe combined to make a functionalized fluorescent dye. Cyclohexylmethylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. Cyclohexylmethyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. Cyclohexylmethyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. Cyclohexylmethyl isothiocyanate and 3-amino-9-ethylcarbazole can becombined to make a functionalized fluorescent dye. 2-piperidinoethylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 2-piperidinoethyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 2-piperidinoethyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 2-piperidinoethylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 2-piperidinoethyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. 2-piperidinoethyl isothiocyanate and 2-aminofluorene can becombined to make a functionalized fluorescent dye. 2-piperidinoethylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. 2-piperidinoethyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 2-piperidinoethyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. 2-piperidinoethyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. p-Tolyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye. p-Tolylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. p-Tolyl isothiocyanate and 1-aminopyrenecan be combined to make a functionalized fluorescent dye. p-Tolylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. p-Tolyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. p-Tolyl isothiocyanate and 2-aminofluorene can be combined to makea functionalized fluorescent dye. p-Tolyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. p-Tolyl isothiocyanate and 1,10-phenanthrolin-5-amine can becombined to make a functionalized fluorescent dye. p-Tolylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. p-Tolyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 2,6-dimethylphenyl isothiocyanate and 1-naphthylaminecan be combined to make a functionalized fluorescent dye.2,6-dimethylphenyl isothiocyanate and 2-aminoanthracene can be combinedto make a functionalized fluorescent dye. 2,6-dimethylphenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 2,6-dimethylphenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.2,6-dimethylphenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye. 2,6-dimethylphenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 2,6-dimethylphenyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. 2,6-dimethylphenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.2,6-dimethylphenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 2,6-dimethylphenyl isothiocyanate and 3-amino-9-ethylcarbazole canbe combined to make a functionalized fluorescent dye. 4-ethylphenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 4-ethylphenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 4-ethylphenyl isothiocyanate and 1-aminopyrene can be combined tomake a functionalized fluorescent dye. 4-ethylphenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.4-ethylphenyl isothiocyanate and 9-aminophenanthrene can be combined tomake a functionalized fluorescent dye. 4-ethylphenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 4-ethylphenyl isothiocyanate and 9-aminoacridine can be combined tomake a functionalized fluorescent dye. 4-ethylphenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 4-ethylphenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 4-ethylphenyl isothiocyanate and 3-amino-9-ethylcarbazole can becombined to make a functionalized fluorescent dye. 4-methoxyphenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 4-methoxyphenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 4-methoxyphenyl isothiocyanate and 1-aminopyrene can be combined tomake a functionalized fluorescent dye. 4-methoxyphenyl isothiocyanateand 6-chrysenamine can be combined to make a functionalized fluorescentdye. 4-methoxyphenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye. 4-methoxyphenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 4-methoxyphenyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. 4-methoxyphenyl isothiocyanate and 1,10-phenanthrolin-5-amine canbe combined to make a functionalized fluorescent dye. 4-methoxyphenylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye. 4-methoxyphenyl isothiocyanateand 3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 2,4-dimethoxyphenyl isothiocyanate and 1-naphthylaminecan be combined to make a functionalized fluorescent dye.2,4-dimethoxyphenyl isothiocyanate and 2-aminoanthracene can be combinedto make a functionalized fluorescent dye. 2,4-dimethoxyphenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 2,4-dimethoxyphenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.2,4-dimethoxyphenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye. 2,4-dimethoxyphenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 2,4-dimethoxyphenyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. 2,4-dimethoxyphenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.2,4-dimethoxyphenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 2,4-dimethoxyphenyl isothiocyanate and 3-amino-9-ethylcarbazole canbe combined to make a functionalized fluorescent dye. 4-chlorophenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 4-chlorophenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 4-chlorophenyl isothiocyanate and 1-aminopyrene can be combined tomake a functionalized fluorescent dye. 4-chlorophenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.4-chlorophenyl isothiocyanate and 9-aminophenanthrene can be combined tomake a functionalized fluorescent dye. 4-chlorophenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 4-chlorophenyl isothiocyanate and 9-aminoacridine can be combinedto make a functionalized fluorescent dye. 4-chlorophenyl isothiocyanateand 1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 4-chlorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 4-chlorophenyl isothiocyanate and 3-amino-9-ethylcarbazole can becombined to make a functionalized fluorescent dye. 2,6-dichlorophenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 2,6-dichlorophenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 2,6-dichlorophenyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 2,6-dichlorophenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 2,6-dichlorophenyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. 2,6-dichlorophenyl isothiocyanate and 2-aminofluorene can becombined to make a functionalized fluorescent dye. 2,6-dichlorophenylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. 2,6-dichlorophenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 2,6-dichlorophenyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. 2,6-dichlorophenyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 2,4,5-trichlorophenyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. 2,4,5-trichlorophenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye. 2,4,5-trichlorophenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 2,4,5-trichlorophenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.2,4,5-trichlorophenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye. 2,4,5-trichlorophenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 2,4,5-trichlorophenyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. 2,4,5-trichlorophenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.2,4,5-trichlorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 2,4,5-trichlorophenyl isothiocyanate and 3-amino-9-ethylcarbazolecan be combined to make a functionalized fluorescent dye. 3-bromophenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 3-bromophenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 3-bromophenyl isothiocyanate and 1-aminopyrene can be combined tomake a functionalized fluorescent dye. 3-bromophenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.3-bromophenyl isothiocyanate and 9-aminophenanthrene can be combined tomake a functionalized fluorescent dye. 3-bromophenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 3-bromophenyl isothiocyanate and 9-aminoacridine can be combined tomake a functionalized fluorescent dye. 3-bromophenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 3-bromophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 3-bromophenyl isothiocyanate and 3-amino-9-ethylcarbazole can becombined to make a functionalized fluorescent dye. 2,5-dibromophenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 2,5-dibromophenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 2,5-dibromophenyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 2,5-dibromophenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 2,5-dibromophenyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. 2,5-dibromophenyl isothiocyanate and 2-aminofluorene can becombined to make a functionalized fluorescent dye. 2,5-dibromophenylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. 2,5-dibromophenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 2,5-dibromophenyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. 2,5-dibromophenyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 2,4,6-tribromophenyl isothiocyanate and 1-naphthylaminecan be combined to make a functionalized fluorescent dye.2,4,6-tribromophenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye. 2,4,6-tribromophenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 2,4,6-tribromophenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.2,4,6-tribromophenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye. 2,4,6-tribromophenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 2,4,6-tribromophenyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. 2,4,6-tribromophenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.2,4,6-tribromophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 2,4,6-tribromophenyl isothiocyanate and 3-amino-9-ethylcarbazolecan be combined to make a functionalized fluorescent dye. 3-fluorophenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 3-fluorophenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 3-fluorophenyl isothiocyanate and 1-aminopyrene can be combined tomake a functionalized fluorescent dye. 3-fluorophenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.3-fluorophenyl isothiocyanate and 9-aminophenanthrene can be combined tomake a functionalized fluorescent dye. 3-fluorophenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 3-fluorophenyl isothiocyanate and 9-aminoacridine can be combinedto make a functionalized fluorescent dye. 3-fluorophenyl isothiocyanateand 1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 3-fluorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 3-fluorophenyl isothiocyanate and 3-amino-9-ethylcarbazole can becombined to make a functionalized fluorescent dye. 2,6-difluorophenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 2,6-difluorophenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 2,6-difluorophenyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 2,6-difluorophenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 2,6-difluorophenyl isothiocyanate and9-aminophenanthrene can be combined to make a functionalized fluorescentdye. 2,6-difluorophenyl isothiocyanate and 2-aminofluorene can becombined to make a functionalized fluorescent dye. 2,6-difluorophenylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. 2,6-difluorophenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 2,6-difluorophenyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. 2,6-difluorophenyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 2,4,6-trifluorophenyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. 2,4,6-trifluorophenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye. 2,4,6-trifluorophenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 2,4,6-trifluorophenyl isothiocyanate and6-chrysenamine can be combined to make a functionalized fluorescent dye.2,4,6-trifluorophenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye. 2,4,6-trifluorophenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 2,4,6-trifluorophenyl isothiocyanate and9-aminoacridine can be combined to make a functionalized fluorescentdye. 2,4,6-trifluorophenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.2,4,6-trifluorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 2,4,6-trifluorophenyl isothiocyanate and 3-amino-9-ethylcarbazolecan be combined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 1-aminopyrene can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 6-chrysenamine can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 9-aminophenanthrene can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 2-aminofluorene can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 9-aminoacridine can becombined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.4-(Trifluoromethyl)phenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 4-(Trifluoromethyl)phenyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 3,5-Bis(trifluoromethyl)phenyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. 3,5-Bis(trifluoromethyl)phenyl isothiocyanate and 2-aminoanthracenecan be combined to make a functionalized fluorescent dye.3,5-Bis(trifluoromethyl)phenyl isothiocyanate and 1-aminopyrene can becombined to make a functionalized fluorescent dye.3,5-Bis(trifluoromethyl)phenyl isothiocyanate and 6-chrysenamine can becombined to make a functionalized fluorescent dye.3,5-Bis(trifluoromethyl)phenyl isothiocyanate and 9-aminophenanthrenecan be combined to make a functionalized fluorescent dye.3,5-Bis(trifluoromethyl)phenyl isothiocyanate and 2-aminofluorene can becombined to make a functionalized fluorescent dye.3,5-Bis(trifluoromethyl)phenyl isothiocyanate and 9-aminoacridine can becombined to make a functionalized fluorescent dye.3,5-Bis(trifluoromethyl)phenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 3,5-Bis(trifluoromethyl)phenyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. 3,5-Bis(trifluoromethyl)phenylisothiocyanate and 3-amino-9-ethylcarbazole can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 1,10-phenanthrolin-5-amine can be combined to make afunctionalized fluorescent dye. 2-Chloro-5-(trifluoromethyl)phenylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye.2-Chloro-5-(trifluoromethyl)phenyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. 4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and2-aminoanthracene can be combined to make a functionalized fluorescentdye. 4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and 1-aminopyrenecan be combined to make a functionalized fluorescent dye.4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and 6-chrysenamine canbe combined to make a functionalized fluorescent dye.4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and 9-aminophenanthrenecan be combined to make a functionalized fluorescent dye.4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and 2-aminofluorene canbe combined to make a functionalized fluorescent dye.4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and 9-aminoacridine canbe combined to make a functionalized fluorescent dye.4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and1,10-phenanthrolin-5-amine can be combined to make a functionalizedfluorescent dye. 4-Bromo-2-(trifluoromethyl)phenyl isothiocyanate and9H-carbazol-2-amine (hydrochloride) can be combined to make afunctionalized fluorescent dye. 4-Bromo-2-(trifluoromethyl)phenylisothiocyanate and 3-amino-9-ethylcarbazole can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 1-naphthylamine can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 2-aminoanthracene can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 1-aminopyrene can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 9-aminophenanthrene can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 2-aminofluorene can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 9-aminoacridine can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 1,10-phenanthrolin-5-amine can be combined to make afunctionalized fluorescent dye. 4-Fluoro-3-(trifluoromethyl)phenylisothiocyanate and 9H-carbazol-2-amine (hydrochloride) can be combinedto make a functionalized fluorescent dye.4-Fluoro-3-(trifluoromethyl)phenyl isothiocyanate and3-amino-9-ethylcarbazole can be combined to make a functionalizedfluorescent dye. 3-Chloro-4-fluorophenyl isothiocyanate and1-naphthylamine can be combined to make a functionalized fluorescentdye. 3-Chloro-4-fluorophenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye.3-Chloro-4-fluorophenyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 3-Chloro-4-fluorophenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 3-Chloro-4-fluorophenyl isothiocyanateand 9-aminophenanthrene can be combined to make a functionalizedfluorescent dye. 3-Chloro-4-fluorophenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 3-Chloro-4-fluorophenyl isothiocyanate and 9-aminoacridine can becombined to make a functionalized fluorescent dye.3-Chloro-4-fluorophenyl isothiocyanate and 1,10-phenanthrolin-5-aminecan be combined to make a functionalized fluorescent dye.3-Chloro-4-fluorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 3-Chloro-4-fluorophenyl isothiocyanate and 3-amino-9-ethylcarbazolecan be combined to make a functionalized fluorescent dye.2-Bromo-4-fluorophenyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye.2-Bromo-4-fluorophenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye.2-Bromo-4-fluorophenyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 2-Bromo-4-fluorophenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 2-Bromo-4-fluorophenyl isothiocyanateand 9-aminophenanthrene can be combined to make a functionalizedfluorescent dye. 2-Bromo-4-fluorophenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 2-Bromo-4-fluorophenyl isothiocyanate and 9-aminoacridine can becombined to make a functionalized fluorescent dye.2-Bromo-4-fluorophenyl isothiocyanate and 1,10-phenanthrolin-5-amine canbe combined to make a functionalized fluorescent dye.2-Bromo-4-fluorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 2-Bromo-4-fluorophenyl isothiocyanate and 3-amino-9-ethylcarbazolecan be combined to make a functionalized fluorescent dye.4-Bromo-2-chlorophenyl isothiocyanate and 1-naphthylamine can becombined to make a functionalized fluorescent dye.4-Bromo-2-chlorophenyl isothiocyanate and 2-aminoanthracene can becombined to make a functionalized fluorescent dye.4-Bromo-2-chlorophenyl isothiocyanate and 1-aminopyrene can be combinedto make a functionalized fluorescent dye. 4-Bromo-2-chlorophenylisothiocyanate and 6-chrysenamine can be combined to make afunctionalized fluorescent dye. 4-Bromo-2-chlorophenyl isothiocyanateand 9-aminophenanthrene can be combined to make a functionalizedfluorescent dye. 4-Bromo-2-chlorophenyl isothiocyanate and2-aminofluorene can be combined to make a functionalized fluorescentdye. 4-Bromo-2-chlorophenyl isothiocyanate and 9-aminoacridine can becombined to make a functionalized fluorescent dye.4-Bromo-2-chlorophenyl isothiocyanate and 1,10-phenanthrolin-5-amine canbe combined to make a functionalized fluorescent dye.4-Bromo-2-chlorophenyl isothiocyanate and 9H-carbazol-2-amine(hydrochloride) can be combined to make a functionalized fluorescentdye. 4-Bromo-2-chlorophenyl isothiocyanate and 3-amino-9-ethylcarbazolecan be combined to make a functionalized fluorescent dye.

While this specification contains many specific implementation details,these should not be construed as limitations on the scope of what may beclaimed, but rather as descriptions of features that may be specific toparticular implementations. Certain features that are described in thisspecification in the context of separate implementations can also beimplemented, in combination, in a single implementation. Conversely,various features that are described in the context of a singleimplementation can also be implemented in multiple implementations,separately, or in any sub-combination. Moreover, although previouslydescribed features may be described as acting in certain combinationsand even initially claimed as such, one or more features from a claimedcombination can, in some cases, be excised from the combination, and theclaimed combination may be directed to a sub-combination or variation ofa sub-combination.

As used in this disclosure, the terms “a,” “an,” or “the” are used toinclude one or more than one unless the context clearly dictatesotherwise. The term “or” is used to refer to a nonexclusive “or” unlessotherwise indicated. The statement “at least one of A and B” has thesame meaning as “A, B, or A and B.” In addition, it is to be understoodthat the phraseology or terminology employed in this disclosure, and nototherwise defined, is for the purpose of description only and not oflimitation. Any use of section headings is intended to aid reading ofthe document and is not to be interpreted as limiting; information thatis relevant to a section heading may occur within or outside of thatparticular section.

As used in this disclosure, the term “about” or “approximately” canallow for a degree of variability in a value or range, for example,within 10%, within 5%, or within 1% of a stated value or of a statedlimit of a range.

As used in this disclosure, the term “substantially” refers to amajority of, or mostly, as in at least about 50%, 60%, 70%, 80%, 90%,95%, 96%, 97%, 98%, 99%, 99.5%, 99.9%, 99.99%, or at least about 99.999%or more.

Values expressed in a range format should be interpreted in a flexiblemanner to include not only the numerical values explicitly recited asthe limits of the range, but also to include all the individualnumerical values or sub-ranges encompassed within that range as if eachnumerical value and sub-range is explicitly recited. For example, arange of “0.1% to about 5%” or “0.1% to 5%” should be interpreted toinclude about 0.1% to about 5%, as well as the individual values (forexample, 1%, 2%, 3%, and 4%) and the sub-ranges (for example, 0.1% to0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range. Thestatement “X to Y” has the same meaning as “about X to about Y,” unlessindicated otherwise. Likewise, the statement “X, Y, or Z” has the samemeaning as “about X, about Y, or about Z,” unless indicated otherwise.

The term “downhole” as used in this disclosure refers to under thesurface of the earth, such as a location within or fluidly connected toa wellbore.

As used in this disclosure, the term “drilling fluid” refers to fluids,slurries, or muds used in drilling operations downhole, such as duringthe formation of the wellbore.

As used in this disclosure, the term “fluid” refers to gases, liquids,gels, and any combination of these, unless otherwise indicated.

As used in this disclosure, the term “subterranean material” or“subterranean zone” or “subterranean formation” refers to any materialunder the surface of the earth, including under the surface of thebottom of the ocean. For example, a subterranean zone or material can beany section of a wellbore and any section of a subterranean petroleum-or water-producing formation or region in fluid contact with thewellbore. Placing a material in a subterranean zone can includecontacting the material with any section of a wellbore or with anysubterranean region in fluid contact the material. Subterraneanmaterials can include any materials placed into the wellbore such ascement, drill shafts, liners, tubing, casing, or screens; placing amaterial in a subterranean zone can include contacting with suchsubterranean materials. In some examples, a subterranean zone ormaterial can be any downhole region that can produce liquid and/orgaseous petroleum materials, water, or any downhole section in fluidcontact with liquid or gaseous petroleum materials, or water. Forexample, a subterranean zone or material can be at least one of an areadesired to be fractured, a fracture or an area surrounding a fracture,and a flow pathway or an area surrounding a flow pathway, in which afracture or a flow pathway can be optionally fluidly connected to asubterranean petroleum- or water-producing region, directly or throughone or more fractures or flow pathways.

As used in this disclosure, “treatment of a subterranean zone” caninclude any activity directed to extraction of water or petroleummaterials from a subterranean petroleum- or water-producing formation orregion, for example, including drilling, stimulation, hydraulicfracturing, clean-up, acidizing, completion, cementing, remedialtreatment, abandonment, aquifer remediation, identifying oil richregions via imaging techniques, and the like.

As used in this disclosure, a “flow pathway” downhole can include anysuitable subterranean flow pathway through which two subterraneanlocations are in fluid connection. The flow pathway can be sufficientfor petroleum and/or water to flow from one subterranean location to thewellbore or vice-versa. A flow pathway can include at least one of ahydraulic fracture, and a fluid connection across a screen, acrossgravel pack, across proppant, including across resin-bonded proppant orproppant deposited in a fracture, and across sand. A flow pathway caninclude a natural subterranean passageway through which fluids can flow.In some implementations, a flow pathway can be a water source and caninclude water. In some implementations, a flow pathway can be apetroleum source and can include petroleum. In some implementations, aflow pathway can be sufficient to divert water, a downhole fluid, or aproduced hydrocarbon from a wellbore, fracture, or flow pathwayconnected to the pathway.

As used in this disclosure, “weight percent” (wt. %) can be considered amass fraction or a mass ratio of a substance to the total mixture orcomposition. Weight percent can be a weight-to-weight ratio ormass-to-mass ratio, unless indicated otherwise.

As used in this disclosure, the abbreviation “MW” refers to molecularweight in daltons.

Particular implementations of the subject matter have been described.Other implementations, alterations, and permutations of the describedimplementations are within the scope of the following claims as will beapparent to those skilled in the art. While operations are depicted inthe drawings or claims in a particular order, this should not beunderstood as requiring that such operations be performed in theparticular order shown or in sequential order, or that all illustratedoperations be performed (some operations may be considered optional), toachieve desirable results. In certain circumstances, multitasking orparallel processing (or a combination of multitasking and parallelprocessing) may be advantageous and performed as deemed appropriate.

Moreover, the separation or integration of various system modules andcomponents in the previously described implementations should not beunderstood as requiring such separation or integration in allimplementations, and it should be understood that the describedcomponents and systems can generally be integrated together or packagedinto multiple products.

Accordingly, the previously described example implementations do notdefine or constrain the present disclosure. Other changes,substitutions, and alterations are also possible without departing fromthe spirit and scope of the present disclosure.

1. A composition comprising: a functionalized fluorescent dye, whereinthe functionalized fluorescent dye comprises anisothiocyanate-containing compound functionalized with a functionalgroup comprising a primary amine, wherein: the isothiocyanate-containingcompound is butyl isothiocyanate, and the functional group is9-aminophenanthrene; the isothiocyanate-containing compound is4-ethylphenyl isothiocyanate, and the functional group is 1-aminopyrene;the isothiocyanate-containing compound is cyclohexylmethylisothiocyanate, and the functional group is 1-naphthylamine; theisothiocyanate-containing compound is 2,6-difluorophenyl isothiocyanate,and the functional group is 2-aminoanthracene; theisothiocyanate-containing compound is hexyl isothiocyanate, and thefunctional group is 6-chrysenamine; the isothiocyanate-containingcompound is ethyl isothiocyanate, and the functional group is1-aminofluorene; the isothiocyanate-containing compound is decylisothiocyanate, and the functional group is 9-aminoacridine; theisothiocyanate-containing compound is benzyl isothiocyanate, and thefunctional group is 1,10-phenanthrolin-5-amine; or theisothiocyanate-containing compound is p-tolyl isothiocyanate, and thefunctional group is 3-amino-9-ethylcarbazole.
 2. The composition ofclaim 1, wherein the isothiocyanate-containing compound is butylisothiocyanate, and the functional group is 9-aminophenanthrene.
 3. Thecomposition of claim 1, wherein the isothiocyanate-containing compoundis 4-ethylphenyl isothiocyanate, and the functional group is1-aminopyrene.
 4. The composition of claim 1, wherein theisothiocyanate-containing compound is cyclohexylmethyl isothiocyanate,and the functional group is 1-naphthylamine. 5.-17. (canceled)
 18. Thecomposition of claim 1, wherein the isothiocyanate-containing compoundis 2,6-difluorophenyl isothiocyanate, and the functional group is2-aminoanthracene.
 19. The composition of claim 1, wherein theisothiocyanate-containing compound is hexyl isothiocyanate, and thefunctional group is 6-chrysenamine.
 20. The composition of claim 1,wherein the isothiocyanate-containing compound is ethyl isothiocyanate,and the functional group is 1-aminofluorene.
 21. The composition ofclaim 1, wherein the isothiocyanate-containing compound is decylisothiocyanate, and the functional group is 9-aminoacridine.
 22. Thecomposition of claim 1, wherein the isothiocyanate-containing compoundis benzyl isothiocyanate, and the functional group is1,10-phenanthrolin-5-amine.
 23. The composition of claim 1, wherein theisothiocyanate-containing compound is p-tolyl isothiocyanate, and thefunctional group is 3-amino-9-ethylcarbazole.